Enantiomerically pure amines as substrates for the Ti‐catalyzed hydroamination of alkynes
Abstract: For two representative reactions employing enantiomerically pure (S)?1?phenylethylamine and (S)-1-cyclohexylethylamine it is shown that Ti-catalyzed hydroamination reactions of alkynes do not generally take place without partial racemization at the chiral center adjacent to the nitrogen at...
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| Main Authors: | , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
13 April 2004
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| In: |
European journal of organic chemistry
Year: 2004, Issue: 9, Pages: 1967-1972 |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/ejoc.200300522 |
| Online Access: | Verlag, Pay-per-use, Volltext: http://dx.doi.org/10.1002/ejoc.200300522 Verlag, Pay-per-use, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.200300522 
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| Author Notes: | Frauke Pohlki, Igor Bytschkov, Holger Siebeneicher, Andreas Heutling, Wilfried A. König, and Sven Doye |
| Summary: | Abstract: For two representative reactions employing enantiomerically pure (S)?1?phenylethylamine and (S)-1-cyclohexylethylamine it is shown that Ti-catalyzed hydroamination reactions of alkynes do not generally take place without partial racemization at the chiral center adjacent to the nitrogen atom. However, identified from a selection of nine Ti catalysts, Cp*2TiMe2 and at least two other catalysts can be used for racemization-free hydroamination reactions of alkynes. Furthermore, the amount of racemization can be reduced significantly by the addition of pyridine to the reaction mixture. |
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| Item Description: | Gesehen am 22.03.2018 |
| Physical Description: | Online Resource |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/ejoc.200300522 |